WO2001021739A1 - Fuel composition with improved lubricity performance - Google Patents
Fuel composition with improved lubricity performance Download PDFInfo
- Publication number
- WO2001021739A1 WO2001021739A1 PCT/EP2000/009147 EP0009147W WO0121739A1 WO 2001021739 A1 WO2001021739 A1 WO 2001021739A1 EP 0009147 W EP0009147 W EP 0009147W WO 0121739 A1 WO0121739 A1 WO 0121739A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fuel composition
- nitrogen
- composition according
- fuel
- exocyclic
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
- C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
Definitions
- This invention relates to fuel compositions of low sulphur content which contain at least one component capable of enhancing the lubricity of such low sulphur fuels.
- Fuels such as diesel are widely used in automotive transport due to their low cost.
- one of the problems with such fuels is the presence of relatively high concentrations of sulphur containing compounds.
- Excessive sulphur contributes to exhaust particulate emissions and can also degrade the effectiveness of some exhaust after-treatment technology which is being introduced in response to regulated limits on exhaust emissions.
- the permitted level of sulphur in diesel fuel has been progressively reduced over the years and further reductions are planned for the future. Whilst reduction in sulphur content can be readily achieved by well known processes such as eg hydrodesulphurisation which is generally carried out in the presence of a catalyst, such process also adversely affects the lubricity of the resultant desulphurised product.
- compositions which are low in sulphur content but are also of the desired lubricity in order to minimise wear and friction and thus protect against damage to the injection system of a diesel engine. It has hitherto been the practice to add anti-wear agents to such formulations including fatty acid esters, lactones, polyoxyalkylene ethers, amino compounds and the like for this purpose.
- anti-wear agents including fatty acid esters, lactones, polyoxyalkylene ethers, amino compounds and the like for this purpose.
- compositions containing compounds such as esters are expensive in terms of both material and storage costs.
- EP-A-0885947 discloses the use of various additives to fuel oil compositions which contain no more than 0.05 wt % of sulphur and having a T 95 of ⁇ 350°C, the additives being (a) an ashless dispersant comprising an acylated nitrogen compound and (b) a monocarboxylic acid having from 2-50 carbon atoms. There is no mention of fused polycyclic amines or of any fuel containing ⁇ 50ppm of sulphur.
- the present invention therefore provides a fuel composition having a sulphur content of not more than 50 ppm by weight and comprising at least 50 ppm based on the total weight of the fuel composition of at least one fused polycyclic aromatic compound which comprises at least one exocyclic group containing nitrogen wherein the nitrogen is attached directly to a ring carbon atom.
- the sulphur content of the fuel composition is preferably less than 50 ppm by weight and more preferably less than 40 ppm by weight.
- Such low sulphur levels can be achieved in a number of ways. For instance, this may be achieved by well known methods such as eg, catalytic hydrodesulphurisation.
- the present invention is
- the base fuels may comprise mixtures of saturated, olefinic and aromatic hydrocarbons and these can be derived from straight run streams, thermally or catalytically cracked hydrocarbon feedstocks, hydrocracked petroleum fractions, catalytically reformed hydrocarbons, or synthetically produced hydrocarbon mixtures.
- the present invention is particularly applicable to diesel fuels that have recently been introduced into the UK market and are generally referred to as ultra-low sulphur automotive diesel oils (hereafter "ULSADO" and is sampled eg from Esso's Fawley Refinery).
- fused polycyclic aromatic compound which has at least one exocyclic group containing nitrogen wherein the nitrogen is attached directly to a ring carbon atom is capable of acting as an antiwear and lubricity enhancing additive for low sulphur fuels according to the invention.
- fused polycyclic aromatic compound as used herein and throughout the specification is meant that said compound comprises an aromatic moiety which has at least two fused rings of which at least one is an aromatic ring, which aromatic ring may in turn be a heterocyclic ring, whether or not the remaining ring(s) in the fused polycyclic structure are aromatic or carry other hydrocarbyl or functional groups such as alkyl, hydroxyl or ketonic or ester groups.
- a cycloaliphatic ring is fused with an aromatic/heterocyclic ring is 1-amino indan and another example is an amino anthraquinone.
- exocyclic amino group may also be attached directly to a carbon atom of a ring which is itself attached to but is not part of the fused polycyclic ring structure.
- the heteroatom may be nitrogen or oxygen.
- the exocyclic group containing nitrogen may be a primary or a secondary amino group and may carry hydrogen and/or hydrocarbyl groups, such hydrocarbyl groups being aliphatic, cycloaliphatic or aromatic in nature and is preferably a primary amino group
- compounds having two exocyclic nitrogen groups are preferable to compounds which have only one exocyclic nitrogen group
- compounds having more than one exocyclic nitrogen group, especially primary amino groups it is even more preferable that these groups are in close proximity and in non-hindered position on the fused polycyclic compound
- the exocyclic nitrogen groups are attached to adjacent carbon atoms, such as eg the 1,2-, 2,3-, 3,4-carbon atoms, or, the 1 ,8-pos ⁇ t ⁇ ons of a binuclear structure of eg the diam o naphthalen
- the amino groups are on adjacent carbon atoms if the fused carbon linking the two rings is ignored
- examples of such compounds containing an exocyclic group containing nitiogen wherein the nitrogen is directly attached to ⁇ ring carbon atom include inter alia 5-am ⁇ no ⁇ ndole, 8-am ⁇ no quinohne, 1 -aminonaphthdlene and 1 ,8-d ⁇ am ⁇ nonaphthalene whereas 2-(2-am ⁇ nophenyl) indole is an example of a compound in which the exocyclic amino group is directly attached to a ring carbon atom wherein the ring itself is attached to a fused polycyclic aromatic compound, le indole
- the fused polycyclic aromatic compound contains at least one secondary amino group
- the hydrocarbyl substituents on this secondary amino group are aliphatic, more preferably a C1-C4 alkyl group
- the composition according to the present invention has enhanced lubricity when compared with fuel compositions which have a low sulphur content but in which the fused polycyclic aromatic compound containing exocyclic nitrogen group is absent
- the amount of the fused polycyclic aromatic compound added to the fuel composition is at least 50 ppm, suitably 70 ppm or more and is preferably from 50-10,000 ppm by weight of the total fuel composition
- the improvement in antiweai and lubricity characteristics of the fuel composition may not bear a linear relationship commensurate with the amount of the fused polycyclic aromatic compound that is added to said composition.
- addition of a vast excess of such an additive may not necessarily continually improve the antiwear or lubricity properties of the fuel composition.
- the fuel composition according to the invention may contain one or more conventional fuel additives, which may be added at the refinery, at the fuel distribution terminal, into the tanker, or as bottle additives purchased by the end user for addition into the fuel tank of an individual vehicle.
- these additives may include cold flow improvers (also known as middle distillate flow improvers), wax antisettling additives, diesel fuel stabilisers, antioxidants, cetane improvers, combustion improvers, detergents, demulsifiers, dehazers, lubricity additives, anti-foamants, anti-static additive, conductivity improvers, corrosion inhibitors, drag reducing agents, reodorants, dyes and markers, and the like.
- the antiwear and lubricity performance of the fuel compositions of the present invention were measured according to the so-called high frequency reciprocating rig test (hereafter referred to as "HFRR").
- HFRR high frequency reciprocating rig test
- the tests are conducted according to the standard procedure published as CEC F-06-A-96 in which a load of 2N (200g) was applied, the stroke length was 1mm, the reciprocating frequency was 50 Hz and sample temperature was 60°C.
- the ambient temperature and humidity were controlled within the specified limits and the calculated value of wear scar diameter was corrected to the standardized water vapour pressure of 1.4 kPa.
- the specimen ball was a grade 28 (ANSIB3.12), AISI E-52100 steel with a Rockwell harness "C” scale (HRC) number of 58-66 (ISO 6508), and a surface finish of less than 0.05 ⁇ m R a
- the lower plate was AISI E-52000 steel machined from anealed rod, with a Vickers hardness "HV30" scale number of 190-210 (ISO 6507/1). It is turned, lapped and polished to a surface finish of 0.02 ⁇ m R a .
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Lubricants (AREA)
- Liquid Carbonaceous Fuels (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/856,115 US6656237B1 (en) | 1999-09-20 | 2000-09-19 | Fuel composition with improved lubricity performance |
EP00960678.1A EP1137746B1 (en) | 1999-09-20 | 2000-09-19 | Use of an additive to improve lubricity performance of a fuel |
JP2001525301A JP2003510408A (en) | 1999-09-20 | 2000-09-19 | Fuel composition with improved lubrication properties |
CA002350955A CA2350955A1 (en) | 1999-09-20 | 2000-09-19 | Fuel composition with improved lubricity performance |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9922234A GB2354254A (en) | 1999-09-20 | 1999-09-20 | Fuel composition with improved lubricity performance |
GB9922234.1 | 1999-09-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001021739A1 true WO2001021739A1 (en) | 2001-03-29 |
Family
ID=10861258
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/009147 WO2001021739A1 (en) | 1999-09-20 | 2000-09-19 | Fuel composition with improved lubricity performance |
Country Status (6)
Country | Link |
---|---|
US (1) | US6656237B1 (en) |
EP (1) | EP1137746B1 (en) |
JP (1) | JP2003510408A (en) |
CA (1) | CA2350955A1 (en) |
GB (1) | GB2354254A (en) |
WO (1) | WO2001021739A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2357296A (en) | 1999-12-16 | 2001-06-20 | Exxon Research Engineering Co | Low sulphur fuel composition with enhanced lubricity |
CN108219874B (en) * | 2017-12-13 | 2020-05-29 | 四川大学 | Tall oil fatty acid compound antiwear agent for ultra-low sulfur diesel oil |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2054276A (en) * | 1934-12-21 | 1936-09-15 | Jr Charles P Wilson | Process and product for the stabilizing of unsaturated hydrocarbons |
US2243168A (en) * | 1937-04-08 | 1941-05-27 | Gasoline Antioxidant Company | Motor fuel product |
US2771367A (en) * | 1953-11-20 | 1956-11-20 | Universal Oil Prod Co | Stabilization of organic compounds |
GB820182A (en) * | 1956-11-14 | 1959-09-16 | British Petroleum Co | Improvements in or relating to the production of gasoline |
EP0487255A1 (en) * | 1990-11-22 | 1992-05-27 | The British Petroleum Company P.L.C. | Composition and process for inhibiting and removing carbonaceous deposits |
WO1994022988A1 (en) * | 1993-04-05 | 1994-10-13 | Mobil Oil Corporation | Improved lubricant performance from additive-treated fuels |
WO1995020637A2 (en) * | 1994-01-31 | 1995-08-03 | Meg S.N.C. Di Scopelliti Sofia & C. | Hydrocarbon oil-aqueous fuel and additive compositions |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2864676A (en) * | 1955-09-29 | 1958-12-16 | Universal Oil Prod Co | Stabilization of organic compounds |
US4863623A (en) * | 1988-03-24 | 1989-09-05 | Texaco Inc. | Novel VI improver, dispersant, and anti-oxidant additive and lubricating oil composition containing same |
GB9502041D0 (en) * | 1995-02-02 | 1995-03-22 | Exxon Chemical Patents Inc | Additives and fuel oil compositions |
GB9621263D0 (en) * | 1996-10-11 | 1996-11-27 | Exxon Chemical Patents Inc | Lubricity additives for fuel oil compositions |
DE69838925T2 (en) * | 1997-04-23 | 2008-12-11 | The Lubrizol Corp., Wickliffe | Diesel fuel compositions |
-
1999
- 1999-09-20 GB GB9922234A patent/GB2354254A/en not_active Withdrawn
-
2000
- 2000-09-19 CA CA002350955A patent/CA2350955A1/en not_active Abandoned
- 2000-09-19 EP EP00960678.1A patent/EP1137746B1/en not_active Expired - Lifetime
- 2000-09-19 US US09/856,115 patent/US6656237B1/en not_active Expired - Lifetime
- 2000-09-19 JP JP2001525301A patent/JP2003510408A/en active Pending
- 2000-09-19 WO PCT/EP2000/009147 patent/WO2001021739A1/en active Application Filing
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2054276A (en) * | 1934-12-21 | 1936-09-15 | Jr Charles P Wilson | Process and product for the stabilizing of unsaturated hydrocarbons |
US2243168A (en) * | 1937-04-08 | 1941-05-27 | Gasoline Antioxidant Company | Motor fuel product |
US2771367A (en) * | 1953-11-20 | 1956-11-20 | Universal Oil Prod Co | Stabilization of organic compounds |
GB820182A (en) * | 1956-11-14 | 1959-09-16 | British Petroleum Co | Improvements in or relating to the production of gasoline |
EP0487255A1 (en) * | 1990-11-22 | 1992-05-27 | The British Petroleum Company P.L.C. | Composition and process for inhibiting and removing carbonaceous deposits |
WO1994022988A1 (en) * | 1993-04-05 | 1994-10-13 | Mobil Oil Corporation | Improved lubricant performance from additive-treated fuels |
WO1995020637A2 (en) * | 1994-01-31 | 1995-08-03 | Meg S.N.C. Di Scopelliti Sofia & C. | Hydrocarbon oil-aqueous fuel and additive compositions |
Also Published As
Publication number | Publication date |
---|---|
US6656237B1 (en) | 2003-12-02 |
EP1137746A1 (en) | 2001-10-04 |
CA2350955A1 (en) | 2001-03-29 |
JP2003510408A (en) | 2003-03-18 |
EP1137746B1 (en) | 2016-04-06 |
GB2354254A (en) | 2001-03-21 |
GB9922234D0 (en) | 1999-11-17 |
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